Se/ZrO2-Catalyzed Oxidation of Phenol

doi:10.6023/cjoc202310020

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1343-1347.DOI: 10.6023/cjoc202310020 Previous Articles Next Articles

氧化锆负载硒催化苯酚氧化反应

雍达明^a^,^*(), 田杰^a, 杨瑞洪^a, 吴启超^a, 张旭^b^,^*()

a 扬州工业职业技术学院化工学院江苏扬州 225127
b 扬州大学化学化工学院江苏扬州 225002

收稿日期:2023-10-23 修回日期:2023-11-27 发布日期:2023-12-15
基金资助:
江苏省自然科学基金(BK20191220); 江苏省高校优秀科技创新团队(2021); 江苏省国际合作项目(BZ2023038); 江苏省高等学校自然科学基金(19KJB210020)

Se/ZrO₂-Catalyzed Oxidation of Phenol

Daming Yong^a(), Jie Tian^a, Ruihong Yang^a, Qichao Wu^a, Xu Zhang^b()

a School of Chemical Engineering, Yangzhou Polytechnic Institute, Yangzhou, Jiangsu 225127
b School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002

Received:2023-10-23 Revised:2023-11-27 Published:2023-12-15
Contact: * E-mail: yongdaming@hit.edu.cn; zhangxu@yzu.edu.cn
Supported by:
Jiangsu Provincial Natural Science Foundation(BK20191220); Jiangsu Provincial Excellent Science and Technology Innovation Team(2021); Jiangsu Province International Cooperation Project(BZ2023038); Natural Science Foundation of the Jiangsu Higher Education Institutions(19KJB210020)

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Abstract

Se/ZrO₂ can be prepared via the reaction of readily available zirconia with NaHSe. The material can catalyze the oxidation of phenol to prepare p-benzoquinone. Compared with traditional selenium-catalyzed oxidation reactions, this reaction does not require the use of chemical oxidants, but can directly utilize molecular oxygen as the oxidant, significantly reducing synthesis costs and being relatively safe. Se/ZrO₂ is a stable selenium-containing material that can be recycled and reused for multiple times without deactivation. Its excellent catalytic oxidation performance is expected to be used in industry.

Key words: selenium, zirconia, catalyzed oxidation, phenol, p-benzoquinone

Cite this article

Daming Yong, Jie Tian, Ruihong Yang, Qichao Wu, Xu Zhang. Se/ZrO₂-Catalyzed Oxidation of Phenol[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1343-1347.

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Fig. & Tab. 4

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Entry	Catalyst	Yield^b/% of 2
1	(PhSe)₂	<5
2	(c-C₆H₁₁Se)₂	8
3	[3,5-(CF₃)₂C₆H₃Se]₂	7
4	(PhSe)₂+CuCl₂ (1∶1)^c	30
5	(PhSe)₂+FeCl₃ (1∶1)^c	22
6	Se/Ag^[11]	29
7	Se/Fe₃O₄^[8]	38
8	Se/CuO	41
9	Se/TiO₂	36
10	Se/Al₂O₃	29
11	Se/SiO₂	22
12	Se/ZrO₂	48

Entry	Catalyst	Yield^b/% of 2
1	(PhSe)₂	<5
2	(c-C₆H₁₁Se)₂	8
3	[3,5-(CF₃)₂C₆H₃Se]₂	7
4	(PhSe)₂+CuCl₂ (1∶1)^c	30
5	(PhSe)₂+FeCl₃ (1∶1)^c	22
6	Se/Ag^[11]	29
7	Se/Fe₃O₄^[8]	38
8	Se/CuO	41
9	Se/TiO₂	36
10	Se/Al₂O₃	29
11	Se/SiO₂	22
12	Se/ZrO₂	48

氧化锆负载硒催化苯酚氧化反应

Se/ZrO₂-Catalyzed Oxidation of Phenol

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Entry	Se amount^b x/mol%	Solvent	T/℃	t/h	Yield^c/%
1	3	THF	60	16	48
2	2	THF	60	16	49
3	1	THF	60	16	32
4	2	Toluene	60	16	23
5	2	Cyclohexane	60	16	20
6	2	MeCN	60	16	36
7	2	DMF	60	16	33
8	2	1,4-Dioxane	60	16	54
9	2	EtOAc	60	16	56
10	2	EtOAc	70	16	60
11	2	EtOAc	Reflux	16	65
12	2	EtOAc	Reflux	18	74
13	2	EtOAc	Reflux	20	82
14	2	EtOAc	Reflux	22	83

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